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Record W2167009844 · doi:10.1021/ja904185b

Hydrogen-Bonding Asymmetric Metal Catalysis with α-Amino Acids: A Simple and Tunable Approach to High Enantioinduction

2009· article· en· W2167009844 on OpenAlexaff
Yingdong Lu, Timothy C. Johnstone, Bruce A. Arndtsen

Bibliographic record

VenueJournal of the American Chemical Society · 2009
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Synthesis and Catalysis
Canadian institutionsMcGill University
Fundersnot available
KeywordsChemistryCatalysisCombinatorial chemistryLigand (biochemistry)SelectivityHydrogen bondBrønsted–Lowry acid–base theoryMetalAmino acidEnantioselective synthesisChiral ligandCopperAlkynylationTransition metalOrganic chemistryMolecule

Abstract

fetched live from OpenAlex

While asymmetric transition-metal catalysis has become a powerful method for constructing chiral products, a challenge in this field is the identification of the correct ligand for high selectivity. We report here a simple approach to chiral catalyst formation: coupling of an available pool of Brønsted acids, namely, amino acid derivatives, with tunable ligands on copper catalysts. This system can be used to generate many different chiral environments simply by changing the amino acid or ligand employed and provides a scaffold for rapid screening and identification of the correct combination for high enantioselectivity. The latter is illustrated in the copper-catalyzed alkynylation of imines in up to 99% ee.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.001
Threshold uncertainty score0.004

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0010.001
Open science0.0010.001
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0010.001

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.008
GPT teacher head0.217
Teacher spread0.209 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations157
Published2009
Admission routes1
Has abstractyes

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